DE1812100B2 - Substituted 1-carbamoyl-2-carbalkoxya minobenzimidazole - Google Patents
Substituted 1-carbamoyl-2-carbalkoxya minobenzimidazoleInfo
- Publication number
- DE1812100B2 DE1812100B2 DE1812100A DE1812100A DE1812100B2 DE 1812100 B2 DE1812100 B2 DE 1812100B2 DE 1812100 A DE1812100 A DE 1812100A DE 1812100 A DE1812100 A DE 1812100A DE 1812100 B2 DE1812100 B2 DE 1812100B2
- Authority
- DE
- Germany
- Prior art keywords
- carbamoyl
- substituted
- minobenzimidazole
- carbalkoxya
- fungal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims 1
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical compound C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 13
- 230000002538 fungal effect Effects 0.000 description 10
- -1 alkyl radical Chemical class 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 235000015097 nutrients Nutrition 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000000417 fungicide Substances 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 238000005245 sintering Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 150000001556 benzimidazoles Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 2
- 241000123650 Botrytis cinerea Species 0.000 description 2
- 241000427940 Fusarium solani Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- XUIIKFGFIJCVMT-LBPRGKRZSA-N L-thyroxine Chemical compound IC1=CC(C[C@H]([NH3+])C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-LBPRGKRZSA-N 0.000 description 1
- WZQNNALXEJBHLB-UHFFFAOYSA-N O.OOO Chemical compound O.OOO WZQNNALXEJBHLB-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- PGXWDLGWMQIXDT-UHFFFAOYSA-N methylsulfinylmethane;hydrate Chemical compound O.CS(C)=O PGXWDLGWMQIXDT-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Description
4.
C-NH-COOR, 4th
C-NH-COOR,
■])■])
NH,NH,
CONH — R,CONH - R,
in der R1 einen Alkylrest mit I bis 3 Kohlenstoffatomen und R2 einen Alkylmercaptoalkylrest mit insgesamt 3 bis 5 Kohlenstoffatomen bedeutet.in which R 1 is an alkyl radical having 1 to 3 carbon atoms and R 2 is an alkyl mercaptoalkyl radical having a total of 3 to 5 carbon atoms.
2. 1 - Methylmercaptoäthylcarbamoyl - 2 - carbomeihoxyaminobenzimidazol. 2. 1 - methylmercaptoethylcarbamoyl - 2 - carbomeihoxyaminobenzimidazole.
3. 1 - Methylmercaptoäthylcarbamoyl - 2 - oArbäthoxyaminobenzimidazol. 3. 1 - methylmercaptoethylcarbamoyl - 2 - oarbethoxyaminobenzimidazole.
4. 1 - Äthylmercaptoäthylcarbamovl - 2 - carbomethoxyaminobenzimidazol. 4.1 - Ethylmercaptoäthylcarbamovl - 2 - carbomethoxyaminobenzimidazole.
5. Fungizide, bestehend aus einem Ben/imida/ol entsprechend Anspruch 1 und einem üblichen festen oder flüssigen Trägerstoff und llilfsstoffen.5. Fungicides consisting of a ben / imida / ol according to claim 1 and a customary solid or liquid carrier and auxiliary substances.
zu Benzimidazole!! der Formelto Benzimidazole !! the formula
3°3 °
Die Erfindung betrifft durch Alkylthioalkyl substituierte 1 - Carbamoyl - 2 - carbalkoxyaminobenzimidazole der allgemeinen FormelThe invention relates to 1-carbamoyl-2-carbalkoxyaminobenzimidazoles substituted by alkylthioalkyl the general formula
C-NH- COOR,C-NH- COOR,
CONH — R,CONH - R,
in der R1 einen Alkylrest mit 1 bis 3 Kohlenstoffatomen und R2 einen Alkylmercaptoalkylrest mit insgesamt 3 bis 5 Kohlenstoffatomen bedeutet und Fungizide, die aus einem Benzimidazol der allgemeinen Formel I und einem üblichen festen oder flüssigen Trägerstoff und Hilfsstoffcn bestehen.in which R 1 denotes an alkyl radical with 1 to 3 carbon atoms and R 2 denotes an alkyl mercaptoalkyl radical with a total of 3 to 5 carbon atoms and fungicides which consist of a benzimidazole of the general formula I and a customary solid or liquid carrier and auxiliaries.
Es ist bekannt, 1 - Butylcarbamoyl - 2 - carbomethoxyamino - benzimidazol und ! - Alkoxyalkyl - earbamoyl - 2 - carbmethoxyamino - benzimidazole (FR-Patcntschrift 15 23 597) als Fungizide zu verwenden. Diese Verbindungen haben den Nachteil, daß sie nur langsam in den eigentlichen Wirkstoff 2-Carbomethoxyaminobenzimidazol übergehen.It is known 1 - butylcarbamoyl - 2 - carbomethoxyamino - benzimidazole and! - alkoxyalkyl - earbamoyl - 2 - carbmethoxyamino - benzimidazole (FR patent specification 15 23 597) to be used as fungicides. These compounds have the disadvantage that they only slowly convert to the actual active ingredient Skip 2-carbomethoxyaminobenzimidazole.
Zur Herstellung der erfindungsgemäßen Verbindungen geht man beispielsweise von einem S-Alkylpseudothioharnstoff aus. der in Form eines Salzes, vorzugsweise als Sulfat, vorliegen kann und setzt ihn mit ein bis zwei Äquivalenten eines Chlorformiats der FormelThe compounds according to the invention are prepared, for example, from an S-alkyl pseudothiourea the end. which can be in the form of a salt, preferably as a sulfate, and sets it with one to two equivalents of a chloroformate of the formula
Cl — C - O - R1 Cl - C - O - R 1
wobei R| die obengenannten Bedeutungen hat. um.where R | has the meanings given above. around.
4545
■N"
H ■ N "
H
NHCO R1
ONHCO R 1
O
N
HN
H
C = NCO R1 OC = NCO R 1 O
in der R1 die oben angegebene Bedeutung hat; die weitere Umsetzung mit Isocyanaten oder Carbaminsäurechloriden führt zu I.in which R 1 has the meaning given above; further reaction with isocyanates or carbamic acid chlorides leads to I.
Die Reaktion mit Isocyanaten kann mit oder ohne Lösungsmittel bei Normaldruck oder erhöhtem Druck innerhalb eines weiten Temperaturbereichs, bevorzugt zwischen 20 und 100"C. vorgenommen werden. Die Reaktion ist nicht an die Verwendung eines bestimmten Lösungsmittels gebunden, doch ist die Verwendung beispielsweise von Pyridin vorteilhaft. Für die Reaktion mit Verbindungen de.-> TypsThe reaction with isocyanates can be carried out with or without a solvent at normal pressure or elevated pressure be carried out within a wide temperature range, preferably between 20 and 100 "C. The The reaction is not tied to the use of any particular solvent, but the use is for example of pyridine advantageous. For reacting with compounds de .-> Type
N'
HN '
H
C-- NHCO-R,C-- NHCO-R,
4040
kommen beispielsweise folgende Isocyanate in Frage:For example, the following isocyanates are possible:
2-Älhylmcrcaptoälhylisocyanat (1).
2-MethylmercaptoäthyIisocyanal (1).2-ethylmcaptoethyl isocyanate (1).
2-methyl mercaptoethyl isocyanal (1).
Die Umsetzung mil Carbaminsäurechloride!! wird vorteilhaft in Gegenwart einer chlorwasserstoffbindenden Verbindung durchgeführt.The implementation with Carbaminsäurechloride !! is advantageous in the presence of a hydrogen chloride Connection carried out.
Nach diesen Verfahren lassen sich beispielsweise die folgenden Wirkstoffe herstellen, z. B.:According to these methods, for example, the following active ingredients can be produced, e.g. B .:
1 - Methylmercaptoälhylcarbamoyl - 2 - carbo methoxyaminoben/imidazol. Sintern >200 C.1 - methylmercaptoethylcarbamoyl - 2 - carbo methoxyaminoben / imidazole. Sintering > 200 C.
zunehmende Z. >265 C. starke Z. >290 C. ! - Methylmercaptoäthylcarbamoyl - 2 - carb-increasing Z.> 265 C. strong Z.> 290 C.! - methylmercaptoethylcarbamoyl - 2 - carb-
äthoxyamiivbenziniidazol. Fp. >270 C (Z.). 1 - Äthylmercaptoäthylcarbamoyl - 2 - carbomelhoxyaminobenzimidazol. Sintern > 200 C,ethoxyamiivbenziniidazole. M.p.> 270 ° C (Z.). 1 - ethyl mercaptoethyl carbamoyl - 2 - carbomelhoxyaminobenzimidazole. Sintering> 200 C,
zunehmende Z. >240 C. starke Z. >280 C, 1 - Älhylmercapioäthylcarbamoyl - 2 - carbäihoxyaminobenzimida/ol. Fp. 289 bis 291 C.increasing temperature> 240 ° C. strong temperature> 280 ° C. 1 - ethylmercapioethylcarbamoyl - 2 - carbäihoxyaminobenzimida / ol. Mp. 289 to 291 C.
Sintern > 255 C.
1 - Melhylmercaptopropylcai'oamoyl - 2 - carh-Sintering> 255 C.
1 - methylmercaptopropylcai'oamoyl - 2 - carh-
äthoxyaminobenziniidazol. Fp. 330 C (Z.).
I - Meihylmercaplopropylcaibiunoyl - 2 - carbomelhoxy;iininobenzimidazo!.
Sintern bei 230 C,ethoxyaminobenziniidazole. M.p. 330 C (Z.).
I - Meihylmercaplopropylcaibiunoyl - 2 - carbomelhoxy; iininobenzimidazo !. Sintering at 230 C,
Fp. 28.Vbis 285 C.Mp. 28.V to 285 C.
Die Wirkstoffe wurden durch Elementaranalysc und UR-Spektroskopie identifiziert.The active ingredients were identified by elemental analysis and UR spectroscopy.
Die eiTmdimgsgemäßen Fungizide können als Lösungen. Emulsionen. Suspensionen oder Stäube-The fungicides according to the specification can be used as Solutions. Emulsions. Suspensions or dust
mittel angewendet werden. Die Anwendungsformen richten sich ganz nach den Verwendungszwecken; sie sollen in jedem Fall eine feine Verteilung der wirksamen Substanz gewährleisten.medium can be used. The forms of application depend entirely on the intended use; they should ensure a fine distribution of the active substance in each case.
Zur Herstellung von direkt versprühbaren Lösungen kommt die Lösung in Wasser in Betracht. Hs können aber auch Kohlenwasserstoffe, wie Tetrahydronaph-Ihalin. und alkyüerie Naphthaline als Spritzflüssigkeiten verwendet werden.The solution in water can be used to produce directly sprayable solutions. Hs can but also hydrocarbons, such as tetrahydronaph-ihalin. and alkyüerie naphthalenes as spray liquids be used.
Wäßrige Anwendungsformen können aus Emulsionskonzentraten. Pasten oder netzbaren Pulvern (Spritzpulvern) durch 7'^iaz von Wasser bereitet werden. Zur Herstellung von Emulsionen können die Substanzen als solche oder in einem Lösungsmittel gelöst mittels Netz- oder Dispergiermitteln, z. B. Polyälhylenoxidartlagerungsprodukte. in Wasser oder organischen Lösungsmitteln homogenisiert werden. Es können aber auch aus wirksamer Substanz. Emulgier- oder Dispergiermittel und eventuelle Lösungsmittel bestehende Konzentrate hergestellt werden, die zur Verdünnung mit Wasser geeignet sind.Aqueous use forms can be obtained from emulsion concentrates. Pastes or wettable powders (Wettable powders) prepared by 7 '^ iaz of water will. To produce emulsions, the substances can be used as such or in a solvent dissolved by means of wetting agents or dispersants, e.g. B. Polyälhylenoxidartlagerungsprodukte. in water or organic solvents are homogenized. But it can also consist of active substances. Emulsifying or concentrates consisting of dispersants and, if appropriate, solvents are suitable for dilution with water.
Stäubemittel können durch Mischen oder gemeinsames Vermählen der wirksamen Subslan/en mil einem festen Trägerstoff, beispielsweise lon. Düngemittel oder Kieselgur, hcniestellt werden.Dusts can be produced by mixing or grinding together the effective subslan / en mil a solid carrier, for example ion. Fertilizers or diatomaceous earth.
Folgende Beispiele erläutern die guten fungiziden Eigenschaften der Wirkstoffe:The following examples explain the good fungicidal properties of the active ingredients:
In der folgenden Tabelle sind die Hemmungswerte gegenüber Botrytis cinerea und Fusarium solani angeführt. Die Wirkstoffe werden in Konzentrationen von 0,002, 0,001 und 0.0001% mit einem 8%igen Biomalzagar gründlich durchmischt. Der Agar wird in Petrischalen mit 9 cm Durchmesser ausgegossen; nach dem Erstarren des Agars werden die Schalen mit Myzelflöckchen von Botrytis cinerea bzw. Fusarium solani zentral beimpft. Die Schalen werden bei 22 bis 25 C bebrütet und nach 8 Tagen wird das Ausmaß der Pilzkolonie-Entwicklung im Vergleich mit den unbehandelten Kontrollen beurteilt.The following table shows the inhibition values against Botrytis cinerea and Fusarium solani. The active ingredients are in concentrations of 0.002, 0.001 and 0.0001% with an 8% bio-malt agar thoroughly mixed. The agar is poured into Petri dishes with a diameter of 9 cm; after When the agar solidifies, the shells are covered with flakes of mycelium from Botrytis cinerea or Fusarium solani inoculated centrally. The dishes are incubated at 22 to 25 C and after 8 days the extent is the development of the fungal colony was assessed in comparison with the untreated controls.
In der Tabelle bedeutetIn the table means
0 = kein Pilzwachstum,0 = no fungal growth,
1 = Durchmesser der Pilzkolonie I bis 2 cm,1 = diameter of the fungal colony I up to 2 cm,
2 = Durchmesser der Pilzkolonie 2 bis 4 cm,2 = diameter of the fungal colony 2 to 4 cm,
3 = Durchmesser der Pilzkolonie 4 bis 5 cm.3 = diameter of the fungal colony 4 to 5 cm.
4 = Durchmesser der Pilzkolonie 5 bis 8 cm,4 = diameter of the fungal colony 5 to 8 cm,
5 = Durchmesser der Pilzkolonie 9 cm.5 = diameter of the mushroom colony 9 cm.
Wirkstoff
N
N
R- Active ingredient
NN R-
C' NHCC) R,C 'NHCC) R,
BolrMiv uncrea
Wirkstoff im NähracarBolrMiv uncrea
Active ingredient in the nutrient car
Fusanuni sokini
Wirkstoff im NiihraizarFusanuni sokini
Active ingredient in the Niihraizar
0.(1112 0.001 0.0001 0.002 O.OOI O.OOO!0. (1112 0.001 0.0001 0.002 O.OOI O.OOO!
R1: CH5 R 1 : CH 5
R2: — CO — NH- CH2 — CH2 — S -- C2H5 R 2 : - CO - NH - CH 2 - CH 2 - S - C 2 H 5
R1 : C2H5 R 1 : C 2 H 5
R2: — CO -NH- CH2 — CH2 — S — CH,R 2 : - CO -NH- CH 2 - CH 2 - S - CH,
R, : CH,R,: CH,
R,: — CO — NH — CH, — CH, — S — C1H,R,: - CO - NH - CH, - CH, - S - C 1 H,
R1": CH,R 1 ": CH,
R2: — CO — NH — CH2 — CH2 — S — CH.,R 2 : - CO - NH - CH 2 - CH 2 - S - CH.,
R, : CH3 R 1 : CH 3
R2: CO — NIl — CW2 — CH2 — S — CH,R 2 : CO - NIl - CW 2 - CH 2 - S - CH,
R, : C2H5 R 1 : C 2 H 5
R2: CO — Nl 1 — CH2 — CH2 — S — CH,R 2 : CO - Nl 1 - CH 2 - CH 2 - S - CH,
Tetra met hylt hi uramdisul fid
Pentachlornitrobenzol (Vergleichsmittel)
Kontrolle (ohne Wirkstoff)Tetra met hylt hi uramdisul fid
Pentachloronitrobenzene (comparative agent)
Control (without active ingredient)
5 55 5
Die Wirkstoffe weiden in einer für das Wachstum des Pilzes Aspergillus niger optimal geeigneten Nährlösung in Mengen von 100, 50, 25, K) und 5 Gcwichtsteilen pro Million Teile Nährlösung zugesetzt. Es werden jeweils 20 ml der so behandelten Nährlösung in 100-ml-F.rlcnmyerkolben mit 0.3 mg AspergillusThe active ingredients graze in a nutrient solution that is ideal for the growth of the Aspergillus niger fungus in quantities of 100, 50, 25, K) and 5 parts by weight added per million parts of nutrient solution. There are in each case 20 ml of the nutrient solution treated in this way in 100-ml-sterile flasks with 0.3 mg Aspergillus
Pilzsporen beimpft. Die Kolben werden 120 Stunden
lang bei 360 C erwärmt und anschließend das Ausmaß der Pilzentwicklung, das bevorzugt auf die Nährlösungsoberlläche
erfolgt, beurteilt.
In der Tabelle bedeutetInoculates fungal spores. The flasks are heated for 120 hours at 360 ° C. and then the extent of fungal development, which preferably occurs on the surface of the nutrient solution, is assessed.
In the table means
0 -- kein Pilzwachslum. abgestuft bis
5 --■ ungehemmtes Pilzwachstum (Pilzdecke auf
der Nührlösimgsoberlläche geschlossen).0 - no mushroom lum. graduated to
5 - ■ uninhibited fungal growth (fungal cover on the nutrient solution surface closed).
WirkstoffActive ingredient
C— NHCO - R,C - NHCO - R,
IlIl
Wirkslnl'fmrnuc in der Niihrlö.Mini!Effective in the nutritive hole mini!
.. . Teile pin Million Teile Niihrlösunj.·... Parts pin million parts nutrient solution.
lim 5(1 25 10lim 5 (1 25 10
C2H5 — CO — NH — CH2 — CH2 - S — C2H5 C 2 H 5 - CO - NH - CH 2 - CH 2 - S - C 2 H 5
C2H, -CO-NH-CH2-CH2-S-CH,C 2 H, -CO-NH-CH 2 -CH 2 -S-CH,
-CO-NH-CH2-CH1-S-C2Hj-CO-NH-CH 2 -CH 1 -SC 2 Hj
— CO — NH — CH, — CH2-CH2 — S — CH,- CO - NH - CH, - CH 2 --CH 2 - S - CH,
-CO-NH-CH2-CH2-S-CH,-CO-NH-CH 2 -CH 2 -S-CH,
C2H5 C 2 H 5
-CO-NH-CH2-CH, -CH2-S-CH, Tct tarnet hyll hi uramidisulfid iVcrgleichsmittc!)-CO-NH-CH 2 -CH, -CH 2 -S-CH, Tct camouflages hyll hi uramidisulphide in comparison with medium!)
Kontrolle (ohne Wirkstoff)Control (without active ingredient)
O 3O 3
4 54 5
4
44th
4th
Zur Prüfung, wie sich verschiedene Benzimidazolderivatc beim Aufbewahren verhalten, wurde folgender Versuch durchgerührt. Die Zersetzung der drei folgenden Verbindungen /u dem unsubstituierlen Grundkörper in Abhängigkeit von der Zeit wurde mil dem Lösungsmittel dcuteriertes Dimethvlsulfoxid Wasser gemessen.To test how various benzimidazole derivatives behave on storage, the following experiment was carried out. The decomposition of the following three compounds / u of the unsubstituted parent structure as a function of time was measured using the solvent-disintegrated dimethyl sulfoxide water.
DI)MSO D1ODI) MSO D 1 O
N NN N
NIK(XCH1 NIK (XCH 1
NH CH1CH1 - RNH CH 1 CH 1 - R
C NIICOOCH,C NIICOOCH,
N' Il BCM IIIN 'Il BCM III
Dabei
ZerfallsIncluded
Decay
R = CH,
R = OCH,
R = SC" H,R = CH,
R = OCH,
R = SC "H,
ergaben sich folgende Halbwertszeiten desthe following half-lives of the
18 Tage.18 days.
IS Tage.IS days.
6 Taue.6 ropes.
Das Ergebnis zeigt, daß die Verbindung Il I im polaren Medium Wasser schneller in BCM übergeht als die Verbindungen I und II. Die Zerfallsdauer von mehreren Tagen ist jedoch noch ausreichend groß, um eine gute Wirkung in der Praxis zu erreichen. Die Verbindung I kann als Transportform des Wirkstoffs BCM in die pflanzliche Zelle angesehen werden.The result shows that the compound II I converts more quickly into BCM in the polar medium water than the compounds I and II. However, the disintegration time of several days is still sufficient great to have a good effect in practice. The connection I can be used as a form of transport of the active ingredient BCM can be viewed in the plant cell.
Je schneller also ein acyliertes Benzimidazol-Derivat (I. Il oder III) nach erfolgter Aufnahme in der Pflanze in BCM übergeht, um so besser muß sein Wirkungseintritt sein.So the faster an acylated benzimidazole derivative (I., II or III) passes into BCM after absorption in the plant, the better its onset of action must be be.
Die WarmblütetTo.xiziläten (LD5n p. o. Maus) liegen bei den bekannten und den neuen Benzimidazolderivuicn über 6400 niü'ku.The warm-blooded toxicity (LD 5n po mouse) for the known and the new benzimidazole derivatives are over 6400 niü'ku.
Claims (1)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681812100 DE1812100C3 (en) | 1968-12-02 | Substituted i-carbamoyl-2-carbalkoxyamlnobenzlmldazoles | |
| SU1382947A SU482930A3 (en) | 1968-12-02 | 1969-11-25 | Fungicide |
| US879937A US3660421A (en) | 1968-12-02 | 1969-11-25 | 1-carbamoyl-2-carbalkoxyamino-benzimidazoles |
| IL33428A IL33428A (en) | 1968-12-02 | 1969-11-25 | Substituted n-benzimidazolyl carbamic acids and their use as fungicides |
| FR6940770A FR2027563A1 (en) | 1968-12-02 | 1969-11-26 | |
| NL6917807A NL6917807A (en) | 1968-12-02 | 1969-11-26 | |
| CH1779769A CH536596A (en) | 1968-12-02 | 1969-11-28 | Process for combating fungi and for preventing fungal attack and fungicidal preparation for carrying out the process |
| SE6916457A SE371198B (en) | 1968-12-02 | 1969-11-28 | |
| OA53798A OA03183A (en) | 1968-12-02 | 1969-12-01 | Substituted benzimidazoles. |
| GB58505/69A GB1287157A (en) | 1968-12-02 | 1969-12-01 | Substituted benzimidazoles |
| BE742452D BE742452A (en) | 1968-12-02 | 1969-12-01 | |
| DK635469AA DK125506B (en) | 1968-12-02 | 1969-12-01 | Fungicide. |
| AT1121169A AT297402B (en) | 1968-12-02 | 1969-12-01 | fungicide |
| ES374142A ES374142A1 (en) | 1968-12-02 | 1969-12-02 | 1-carbamoyl-2-carbalkoxyamino-benzimidazoles |
| MY211/73A MY7300211A (en) | 1968-12-02 | 1973-12-30 | Substituted benzimidazoles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681812100 DE1812100C3 (en) | 1968-12-02 | Substituted i-carbamoyl-2-carbalkoxyamlnobenzlmldazoles |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1812100A1 DE1812100A1 (en) | 1970-06-11 |
| DE1812100B2 true DE1812100B2 (en) | 1976-01-02 |
| DE1812100C3 DE1812100C3 (en) | 1976-08-05 |
Family
ID=
Also Published As
| Publication number | Publication date |
|---|---|
| BE742452A (en) | 1970-06-01 |
| FR2027563A1 (en) | 1970-10-02 |
| AT297402B (en) | 1972-03-27 |
| DE1812100A1 (en) | 1970-06-11 |
| IL33428A0 (en) | 1970-01-29 |
| MY7300211A (en) | 1973-12-31 |
| SE371198B (en) | 1974-11-11 |
| US3660421A (en) | 1972-05-02 |
| NL6917807A (en) | 1970-06-04 |
| IL33428A (en) | 1972-12-29 |
| DK125506B (en) | 1973-03-05 |
| ES374142A1 (en) | 1972-03-16 |
| CH536596A (en) | 1973-05-15 |
| OA03183A (en) | 1970-12-15 |
| SU482930A3 (en) | 1975-08-30 |
| GB1287157A (en) | 1972-08-31 |
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|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8330 | Complete renunciation |